HCID 178491329, compound → HCID 178491328, compound

HRID 392207Notes

Reaction equation

HRID 392207 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]3[C:12]([CH2:13][OH:14])=[CH:11][CH:10]=[C:9]([O:15][CH3:16])[C:7]=3[N:8]=2)[CH2:3][CH2:2]1>C1(C)C=CC=CC=1.ClCCl.[O-2].[O-2].[Mn+4]>[CH:1]1([C:4]2[NH:5][C:6]3[C:12]([CH:13]=[O:14])=[CH:11][CH:10]=[C:9]([O:15][CH3:16])[C:7]=3[N:8]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 1

HCID 178491329HCID 178491329, compound

Product 1

HCID 178491328HCID 178491328, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

A stirred suspension of 2-cyclopropyl-7-methoxy-3H-benzimidazole-4-methanol [7.73 g, Reference Example 22(a)] in a mixture of toluene (250 ml) and dichloromethane (150 ml), at room temperature and under nitrogen, was treated portionwise with activated manganese dioxide (11 g). The resulting suspension was stirred under nitrogen at 85° C. for 3 hours. The suspension was allowed to cool slightly and was then filtered through hyflosupercel washing the filter pad six times with hot ethyl acetate (50 ml). The combined filtrate and washings were dried over magnesium sulphate and then evaporated to yield the title compound as a cream coloured powder (7.26 g).

Workup

  1. temperatureto cool slightly
  2. filtrationwas then filtered through hyflosupercel
  3. washwashing the filter pad six times with hot ethyl acetate (50 ml)
  4. dry with materialThe combined filtrate and washings were dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-ab96f69c78b0422faed646636b107787
Source dataset
uspto-grants-2004_10
Patent number
US06800645B1

Reaction notes

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